3-(Dimethylamino)pyrrolidine → N-[2-Chloro-5-(2'-methylamino-[3,4']bipyridinyl-2-yloxy)-phenyl]-2-(3-dimethylamino-pyrrolidin-1-yl)-5-trifluoromethyl-benzamide

HRID 1361690Notes

Reaction equation

HRID 1361690 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH3:22])[CH:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[NH:23][C:24](=[O:36])[C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1F.[CH3:37][N:38]([CH3:44])[CH:39]1[CH2:43][CH2:42][NH:41][CH2:40]1>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH3:22])[CH:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[NH:23][C:24](=[O:36])[C:25]1[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=[CH:27][C:26]=1[N:41]1[CH2:42][CH2:43][CH:39]([N:38]([CH3:44])[CH3:37])[CH2:40]1

Participants

4

Reactant 2

HCID 27585193-(Dimethylamino)pyrrolidineHCID 58588060HCID 58588060, compound

Product 1

HCID 66970539N-[2-Chloro-5-(2'-methylamino-[3,4']bipyridinyl-2-yloxy)-phenyl]-2-(3-dimethylamino-pyrrolidin-1-yl)-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

N-[2-Chloro-5-(2′-methylamino-[3,4′]bipyridinyl-2-yloxy)-phenyl]-2-fluoro-5-trifluoromethyl-benzamide (65 mg, 0.13 mmol) and dimethyl-pyrrolidin-3-yl-amine (22 mg, 0.189 mmol) were dissolved in 0.3 mL DMSO. The solution was heated to 80° C. and stirred for 22 h. The reaction was then cooled to RT, quenched with water, extracted into EtOAc, washed twice with water, once with brine, dried over Mg2SO4, filtered, and concentrated in vacuo to yield a crude mixture that was purified by preparative TLC (10% MeOH/CH2Cl2) to give the title compound as an off-white solid. MS m/z (M+H)+=611; Calc'd 611.06 for C31H30ClF3N6O2.

Workup

  1. temperatureThe reaction was then cooled to RT
  2. customquenched with water
  3. extractionextracted into EtOAc
  4. washwashed twice with water, once with brine
  5. dry with materialdried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield a crude mixture that
  9. customwas purified by preparative TLC (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-877357f11f8844138deedf9429ee9436
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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